Methanesulfonamide → Tert-butyl [(2-isobutyl-4-(4-methylphenyl)-6-{2-[(methylsulfonyl)amino]-2-oxoethoxy}quinolin-3-yl)methyl]carbamate

HRID 1986436ノート

反応式

HRID 1986436 の反応式
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[C:11]([CH2:32][CH:33]([CH3:35])[CH3:34])=[N:12][C:13]2[C:18]([C:19]=1[C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)=[CH:17][C:16]([O:27][CH2:28][C:29](O)=[O:30])=[CH:15][CH:14]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N(OC(ON2C(=O)CCC2=O)=O)C(=O)C1.[CH3:54][S:55]([NH2:58])(=[O:57])=[O:56].C1CCN2C(=NCCC2)CC1>CN(C)C=O.O>[CH2:32]([C:11]1[C:10]([CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[C:19]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:27][CH2:28][C:29]([NH:58][S:55]([CH3:54])(=[O:57])=[O:56])=[O:30])[CH:17]=2)[N:12]=1)[CH:33]([CH3:35])[CH3:34]

参加物

7

反応物 4

HCID 72879MethanesulfonamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 676246Di(succinimido) carbonateHCID 68829615{[3-{[(Tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]oxy}acetic acid

生成物 1

HCID 69152932Tert-butyl [(2-isobutyl-4-(4-methylphenyl)-6-{2-[(methylsulfonyl)amino]-2-oxoethoxy}quinolin-3-yl)methyl]carbamate収率 100.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of {[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]oxy}acetic acid (0.25 g, 0.52 mmol) in N,N-dimethylformamide (5 ml) was added di(N-succinimidyl) carbonate (0.42 g, 2.6 mmol), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture were added methanesulfonamide (0.25 g, 2.6 mmol) and 1,8-diazabicyclo[5.4.0]-7-undecene (0.40 ml, 2.6 mmol), and the mixture was stirred at 100° C. for 5 hrs. The reaction mixture was cooled to room temperature and water was poured thereinto. The mixture was extracted with ethyl acetate and the extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was crystallized from n-hexane-diisopropyl ether to give tert-butyl [(2-isobutyl-4-(4-methylphenyl)-6-{2-[(methylsulfonyl)amino]-2-oxoethoxy}quinolin-3-yl)methyl]carbamate (0.29 g, yield 98%) as pale-yellow crystals.

後処理

  1. stirringthe mixture was stirred at 100° C. for 5 hrs
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was crystallized from n-hexane-diisopropyl ether

出典と根拠

ORDレコード
ord-0d1893f1eff04ee09fbc4f021986b1d5
出典データセット
uspto-grants-2009_06
特許番号
US07547710B2

反応ノート

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